Hair dye protective agent

ABSTRACT

A protective agent for hair dyes to prevent fading of the dye because of the action of sunlight or other factors. This agent is a reaction product of either acrylonitrile or a mixture of acrylonitrile-benzophenone and an oxy-substituted benzophenone with phenacetin. The proportion of the two reactants may vary from about 3:1 to about 200:1 parts by weight of the acrylonitrile or acrylonitrile-benzophenone mixture relative to the phenacetin.

United States Patent Akrongold et al.

[54] HAIR DYE PROTECTIVE AGENT [72] Inventors: Harold S. Akrongold; Rochelle Akrongold, both of 39 Cathay Rd., East Rockaway, Long Island; Michael Goldsmith, 509 Madison Avenue, New York, all of N.Y.

[22] Filed: June 18, 1970 [21] Appl. No.: 47,605

[52] US. Cl ..260/465.9, 260/465 D, 424/47 [51] Int. Cl. ..C07c 121/32, C07c 121/52 [58] Field of Search ..260/465.9, 465 D; 424/47 [56] References Cited OTHER PUBLICATIONS C.A., Vol. 64, (1966), Schwarzkopf, pp. 4860- 4861 51 Aug. 8, 1972 Primary Examiner-.loseph P. Brust Attorney-Arthur A. Jacobs [57] ABSTRACT 2 Claims, No Drawings This invention relates to a protective agent for dyes, and it particularly relates to a protective agent for hair dyes.

The color of dyed hair is subject to fading when exposed to the sun or other source of ultra-violet rays for a significant length of time. For example, black hair has a tendency to assume a reddish coloration due to fading of the dye by the action of the ultra-violet rays. Fading may also be caused by normal exogenous contactants or by a number of endogenous factors.

It is the primary object of the present invention to provide a coating for dyed hair which is resistant to fading ordinarily caused by the action of any single type of source, such as ultraviolet rays or exogenous or endogenous factors.

Another object of the present invention is to provide a coating of the aforesaid type that is relatively inexpensive, easy to formulate, and simple to use.

In accordance with the present invention, the above and other objects are achieved by utilizing the reaction product of (a) either acrylonitrile or a mixture of acrylonitrile and an oxy-substituted benzophenone with (b) phenacetin.

The proportion of the two reactants may vary between about 3:1 and about 200:1 parts by weight of the acrylonitrile or acrylonitrile-benzophenone mixture relative to the phenacetin. The reaction may take place between about 40 and 75 C.

When the acrylonitrile-oxy-substituted benzophenone mixture is used, the ratio of the two components may vary between about 100:1 and 2:1 parts by weight of the acrylonitrile relative. to the oxysubstituted benzophenone, although the ratio of the total mixture relative to the phenacetin remains as indicated above.

Among the substituted benzophenones utilizable'in this invention are 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5- sulfonic acid, 2,2 -dihydroxy-4-n-octoxybenzophenone and 2-hydroxy-4-n-octylbenzophenone. The products of this type made by General Aniline & Film Corp., under the name U- vinul are most satisfactory for the purpose.

The following examples illustrate the present invention but are not intended to limit it except as claimed:

EXAMPLE 1 100 grams of acrylonitrile were heated to 50C., after which 5 grams of phenacetin were slowly added over a period of one-half hour, while maintaining constant agitation. At the end of this period, the temperature was raised to 65 C. and then maintained for 5 minutes or until the reaction was complete. The temperature was then slowly lowered to room temperature over a period of one-half hour. The resultant product was a viscous yellow oil. 7

EXAMPLE 2 100 grams of acrylonitrile was mixed with 20 grams of Uvinul N-539" (General Aniline & Film Corp.), a light, yellow liquid with a melting point of lC., a boiling point of 200 C. and a specific gravity of 1.0478. After these components were thoroughly mixed, 7 grams of phenacetin were slowly added and the same reaction, including temperatures and times, was carried out as in Example 1. The same reaction and proportions may be used with any of the substituted benzophenones specifically set forth above.

The products of both Examples 1 and 2 are viscous oils which may be applied directly to the dyed hair by working it into the hair in the same manner as any ordinary hair dressing, or it may be used in a liquid or aerosol spray.

The products of this invention may be combined with any standard hair spray polymer such as PVP (polyvinylpyrrolidone), or one of the so-called Gan trez" resins (General Aniline & Film Corp.), or the soca1led"Nationa1 Starch resins. The ratio of reaction product to the polymer may be between about 10:1 and 1:10 percent by weight of the reaction product relative to the polymer. One such spray composition is as follows:

EXAMPLE 3 1.3 parts by weight PVP is mixed with 1.6 parts by weight of the reaction product of Example 2, and 97.1 parts by weight of ethyl alcohol (FDA 40 anhydrous) is then added. The components are then thoroughly mixed to form the finished spray. This composition is formed at room temperature.

The product made with the acrylonitrile itself extends the time of satisfactory exposure period of the dyed hair to about twice that when the present coating is not used. However, a product made with the mixture of acrylonitrile and the oxy-substituted benzophenone extends the satisfactory period of exposure to about 15 times that of untreated dyed hair. In this respect, hair dyed black with p-phenylenediamine in the standard manner was found to exhibit a reddish tinge after 1 56 hours in strong sunlight. The same type dyed hair, when coated with a product formed in accordance with the present invention, and utilizing only the acrylonitrile reactant, didmot exhibit any reddish tinge until 3 A hours of exposure to the same sunlight. The same type dyed hair, when coated with a product of the present invention made with the acrylonitrile-substituted benzophenone mixture, did not exhibit any reddish tinge for 22 hours.

The invention claimed is:

1. A reactionproduct formed by the reaction of (a) either acrylonitrile or a mixture of acrylonitrile and an oxy-substituted benzophenone wherein the proportion of acrylonitrile to oxy-substituted benzophenone is between about 100:1 and 2:1 parts by weight, and (b) phenacetin, reactants (a) and (b) being in a proportion of between about 3:1 and 200:1 parts by weight, and the reaction taking place at a temperature of between about 40-75 C., said oxy-substituted benzophenone being selected from the group consisting of 2,2 dihydroxy 4,4 -dimethoxybenzophenone; 2 hydroxy 4 -methoxybenzophenone 5 sulfonic acid; 2,2 dihydroxy 4 -n octoxybenzophenone; and 2 hydroxy 4 -n -octylbenzophenone.

2. The product of claim 1 wherein reactant (b) is added to reactant (a) under constant agitation while the temperature is lower than the boiling point of the reactants, said boiling point being above C., then raising the temperature to a point still below said boiling point, and within the range of 40-75 C., maintaining the last-mentioned temperature until the reaction is complete, and thereafter lowering the temperature to room temperature. 

2. The product of claim 1 wherein reactant (b) is added to reactant (a) under constant agitation while the temperature is lower than the boiling point of the reactants, said boiling point being above 75*C., then raising the temperature to a point still below said boiling point, and within the range of 40*-75* C., maintaining the last-mentioned temperature until the reaction is complete, and thereafter lowering the temperature to room temperature. 